Over the course of the past few months, I’ve told this story repeatedly as I’ve met a lot of amazing engineers, founders and investors in Seattle. I thought it would be interesting to capture this in a post and come back to it down the road.

I’ve frequently encountered the question, “So, how did you do it?” In this case, “it” refers to starting Mobilisafe and securing funding from some great investors. I’ve oversimplified my response at times, indicating that I got lucky raising money with a slide deck and a prototype. The reality is that while luck has something to do with it, there is quite a bit more to it than that.

Early Stage Startup Experience

When I was in college, a startup called 4thpass in Seattle contacted me about an internship opportunity. It was a small company at the time with only 10 people and they had recently raised $8 million from a local investor. I went in for an interview during spring break at a cramped and messy office at 4th and Union in Seattle and came away wondering what the heck had just happened. The questions were the hardest I’d encountered, the team was extremely diverse and compelling and to my surprise, I had a lot of fun.

While my peers were taking internships at Microsoft, Oracle and IBM, I gravitated toward the opportunity at 4thpass. I remember doing a dollars and cents analysis and realizing that the difference in earnings was marginal and that it was only one summer and there were other internsihps ahead of me to do something more traditional like my peers. At the time, I didn’t realize that making that decision would significantly change my life. I ended up staying with 4thpass through its sale to Motorola and still count early team members as friends.

Keetli – Strike One

One of the 4thpass founders contacted me in late 2007 about a startup idea he was working on. He had stayed on at Motorola for several years after the acquisition and had recently left. I had been tossing around some of my own ideas and when we met to discuss what he was looking into, there was quite a bit of overlap so we decided to work together.

The Keetli experience for me was full of learning. Our founding team was composed of 4 people and three of us worked on it part-time while the main founder/CEO worked on it full-time. While I was still living in the SF Bay Area, the rest of the founding team was in Chicago. I ended up traveling quite a bit in 2008 as we worked to get Keetli off the ground. We were focused on improving the personal digital media workflow, moving it from a computer-centric experience to a TV-centric experience. It was a very ambitious project, with hardware and software products, and required a lot of capital to really get things going.

I learned many lessons from my Keetli experience including these:

• Capital requirements: Hardware-related businesses are so capital intensive that you must have a very unique circumstance to have a viable path forward. That uniqueness could be relationships, knowledge, experience, etc. While we did have some of that with our team, it was not enough for us to get there.
• Distribution is critical: This is even more important in a hardware-related business. Even though we spent a lot of time on this issue, I still feel in hindsight that we barely scratched the surface of understanding how to achieve a distribution model that was viable. A lot of startups overlook how important this is.
• Fundraising is hard: We had connections to VCs at some great firms and could get meetings based on the moderately successful exit of 4thpass. Getting a meeting with an investor turns out to not really be the problem in fundraising. I attended many of the fundraising discussions and saw the kinds of questions being asked, some of which we were completely unprepared for. We also ran into issues with macro trends as the capital markets in 2008 got worse faster than we could close on terms.
• Commitment: Every founder needs to be roughly equally committed. Some of us being part-time and one of us being full-time made achieving progress on different fronts very difficult. I believe there was some frustration that built up as a result of the varying committments.
• Balance execution against being nimble: We spent quite a bit of time trying to find our direction and ended up reacting too much to competition. Since our solution was end to end, hardware and software, all the moving pieces made us susceptible to this. We unfortunately erred on the side of over thinking that which created an analysis paralysis problem that ground our execution to a halt. Keeping our founding team smaller would have helped considerably with this.

IntuitiveWerks – Strike Two

When I joined T-Mobile, I was fortunate to work with a great peer there, Dirk Sigurdson, who is now my co-founder at Mobilisafe. He and I gained mutual respect for each other and occasionally talked about working on a startup together. I can’t remember how exactly, but I learned about the Founder Institute program and convinced Dirk to sign up with me. At the time I figured it would be worthwhile because of the emphasis on meeting with and learning from successful entrepreneurs. I had formed IntuitiveWerks previously and we repurposed it for investigating our ideas through Founder Institute.

Ultimately we didn’t cultivate something that we believed was worth pursuing to complete the Founder Institute program. Immediately after the program, it felt like a second strike, but in hindsight, the program was great batting practice. We got a lot of intense practice on all aspects of getting a business off the ground including generating and validating ideas and pitching. The most important thing that came out of it was that Dirk and I got to practice working together on something outside of a typical corporate environment. Incidentally, the inaugural Seattle batch for Founder Institute brought together some great entrepreneurs who have gone on to start Massively Fun, MemeTales, Apptentive and Puzzazz among other promising companies.

Getting On Base

I got some advice early on from one of the 4thpass founders: Go with what you know. When we folded Keetli, I knew that at some point I would get back to something entrepreneurial because the experience was amazing for me in spite of its failure. When I shelved IntuitiveWerks, I was disappointed but felt like I was getting closer. Something was still missing and I couldn’t put my finger on it yet.

Last summer, I spent a considerable amount of time contemplating what move would be next for me. I had the conviction to go start something, but I wanted to learn a bit more from my job at the time before venturing out on my own. I spent more time with T-Venture, the venture capital arm of Deutsch Telekom which is T-Mobile’s parent company where we enjoyed a mutually beneficial relationship: I helped with providing feedback on startups while learning how they viewed different investment opportunities.

What was common to many of the startups I met with were founders that had some domain expertise prior to starting a company in that area that gave them unique insight. While there are some amazing exceptions to this pattern, I started to go back and think through the experience I had and zeroed in on a unique body of mobile and security experiences.

I’ll detail this more in a future post, but last fall I cultivated a few ideas and was fortunate that my first VC meeting was a casual conversation with a storied investor at one of the best firms. His feedback was that I was the kind of person he would love to back. While we ultimately didn’t find a way to work together for the initial round of funding for Mobilisafe, that feedback bolstered my self confidence and I began to believe with more conviction that I was credible to get this company off the ground.

Final Thoughts

Getting funding wasn’t an endgame but it is providing us with a means to get to an end. While there are some arbitrary things that can make or break a startup crossing the chasm from idea to getting funding, there are some experiential things that can help make this a more deterministic process. I’ve tried to touch on some things about my experiences that I believe were critical in hindsight. While it may be in vogue to start a company without much or any professional experience, for the rest of us out there, getting some requisite experience under your belt if you don’t have it (we’re hiring) can help get you on your way.